Benzylamine → HCID 19781434, compound

HRID 257743Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:21])[CH:5]=[CH:6][CH2:7][CH2:8][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11](C(=O)C)[CH:10]=1)[CH3:2].[CH2:22]([NH2:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>>[CH2:1]([O:3][C:4](=[O:21])[CH2:5][CH:6]([CH2:7][CH2:8][C:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[NH:11][CH:10]=1)[NH:29][CH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH3:2]

Participants

Reactant 2

HCID 7504Benzylamine

HCID 53953280Ethyl 5-(1-acetyl-1H-indol-3-yl)pent-2-enoate

Product 1

HCID 19781434HCID 19781434, compoundYield 79.9%

Conditions

Temperature: 80 °C

Procedure

A mixture of olefin 32 (5.0 g, 17.5 mmol) and benzylamine (7.7 mL, 70 mmol) was heated at 80° C. for 20 hours. The cooled reaction mixture was applied directly to a flash chromatography column (silica, 30% ethyl acetate/hexanes) to give the Micheal adduct 33 (4.9 g) as a viscous yellow oil.

Workup

customThe cooled reaction mixture

Sources & evidence

ORD record: ord-ed2f5ef2241f4f2b9cb1f01ad77386a7
Source dataset: uspto-grants-1993_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05264420

Reaction notes

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